Hydrophilic modifications in peptide nucleic acid — Synthesis and properties of PNA possessing 5-hydroxymethyluracil and 5-hydroxymethylcytosine
Hydrophilic modifications in peptide nucleic acid — Synthesis and properties of PNA possessing 5-hydroxymethyluracil and 5-hydroxymethylcytosine
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肽核酸的亲水修饰——具有5-羟甲基尿嘧啶和5-羟甲基胞嘧啶的PNA的合成和性质
DOI：
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发表时间：
2007
期刊：
影响因子：
--
通讯作者：
F. Wojciechowski
中科院分区：
文献类型：
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作者：
R. Hudson;Yuhong Liu;F. Wojciechowski
我们已经调查了化学C5-羟甲基-尿嘧啶和-胞嘧啶在肽核酸（PNA）和随后的影响，这种修饰对PNA杂交行为的纳入。在文献研究的基础上，我们制备了一种适合于Fmoc寡肽合成的含5-羟甲基尿嘧啶的肽核酸单体。开发了一种改进的大规模合成5-羟甲基胞嘧啶的方法，作为合成含有该核碱基的单体的起点。在每种情况下，羟基被封端为叔丁基二苯基甲硅烷基醚，胞嘧啶的环外氨基被苯甲酰基另外封端。使用标准方案将修饰的单体掺入寡聚体序列中的分离位置。修饰后的寡聚体表明5-羟甲基与三链体和双链体的形成是相容的。关键词：肽核酸，羟甲基尿嘧啶，羟甲基胞嘧啶，修饰的核酸。
We have investigated the chemistry for the incorporation of C5-hydroxymethyl-uracil and -cytosine in peptide nucleic acid (PNA) and the subsequent effect of this modification on PNA hybridization behavior. Largely based on literature precedent, we prepared a peptide nucleic acid monomer, possessing 5-hydroxymethyuracil, which was compatible with Fmoc-based oligopeptide synthesis. An improved, large-scale synthesis of 5-hydroxymethylcytosine was developed, as a starting point for the synthesis of a monomer containing this nucleobase. In each case, the hydroxyl group was blocked as a t-butyldiphenylsilyl ether, and the exocyclic amino group of cytosine was additionally blocked with the benzoyl-group. The modified monomers were incorporated into isolated positions in the oligomer sequence using standard protocols. The modified oligomers showed that the 5-hydroxymethyl group is compatible with triplex and duplex formation.Key words: peptide nucleic acid, hydroxymethyluracil, hydroxymethylcytosine, modified nu...
影响因子：
4.1
作者：
LaFrancois, CJ;Fujimoto, J;Sowers, LC
通讯作者：
Sowers, LC
细胞渗透性肽核酸的合成及其杂交和摄取特性的表征。
DOI：
10.1016/j.bmcl.2006.06.052
发表时间：
2006
期刊：
Bioorganic & medicinal chemistry letters.
影响因子：
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作者：
Zhou,Peng;Dragulescu-Andrasi,Anca;Bhattacharya,Birendra;O'Keefe,Heather;Vatta,Paolo;Hyldig-Nielsen,JensJ;Ly,DanithH
通讯作者：
Ly,DanithH
影响因子：
14.9
作者：
TardyPlanechaud, S;Fujimoto, J;Sowers, LC
通讯作者：
Sowers, LC